Top Tech Jobs & Startup Jobs in Chicago, IL

Build and ship end-to-end features for a restaurant operating system, lead architecture and technical execution, define product roadmap with cross-functional teams, and maintain high-quality CI/CD and productionized systems.

Design, implement, test, release, and maintain scalable iOS application features. Collaborate with engineering and product teams, optimize application performance, produce documented code, estimate work, and maintain CI/CD pipelines. Requires strong Swift, SwiftUI, UIKit, concurrency, REST API, testing, Git, App Store submission, and continuous delivery experience.

Own the agent orchestration platform and co-lead AI agent solutions across the insurance lifecycle. Define agent roadmaps, prompts, tools, autonomy tiers, evaluation datasets, governance, rollout gates, observability, and cost controls. Partner with product, engineering, data, and experience teams to translate business needs into agent specifications and measurable outcomes. Establish regression testing, human escalation policies, audit trails, and production quality standards for LLM-powered products.

Lead and scale the Art function across multiple live-service games. Coach Art Leads, oversee visual direction, manage art capacity and resources, establish quality standards and workflows, lead hiring, and partner with product, production, engineering, and executive teams to deliver high-quality art across diverse games without sustained crunch.

Prepare accurate tax returns for LLCs and S Corporations, manage financial records, input data into tax software, onboard clients, and collaborate with bookkeeping staff. The role requires client-focused tax preparation experience, strong attention to detail, virtual-work adaptability, and proficiency with ProConnect, QuickBooks Online, Microsoft Word, and Microsoft Suite.

Lead and mentor a team of engineers while contributing hands-on to complex features. Define architecture, drive development best practices, conduct code reviews, coordinate cross-functional requirements, and ensure timely delivery of high-quality ecommerce marketplace software.

Build and maintain core products and collaborate on larger consulting projects using TypeScript, Python, FastAPI, Next.js, GCP, and generative AI frameworks. The role involves hands-on software development within a rapidly growing, remote team serving Saudi Arabia and the GCC.

Leads global client engagements focused on leadership development, including designing and delivering executive workshops, advising organizations on leadership systems, developing thought leadership, managing client relationships, and mentoring consultants. The role requires extensive professional services or coaching experience, strong facilitation and project management skills, advanced personal contemplative practice, and the ability to work effectively with senior stakeholders in a virtual international environment.

Lead and support customer implementations of Amtech ERP software, including requirements gathering, solution configuration, process documentation, testing, user training, troubleshooting, and go-live support. Partner with customers on solution design, deliver ERP knowledge transfer, identify delivery risks, support proposals and presales activities, and contribute to implementation standards, process improvement, and peer mentoring. Travel up to 50% is required.

Leads Intradiem’s Technical Support organization, owning post-go-live customer experience, support strategy, operating models, SLAs, escalations, staffing, and performance. Drives AI transformation, automation, continuous improvement, platform migration support, critical incident response, customer communications, root-cause analysis, and compliance. Develops multilevel technical teams, manages outsourced support partners, and collaborates with Implementation, Customer Success, Product, and Engineering. Requires extensive technical support leadership experience in SaaS environments, including integrations, APIs, cloud platforms, AI support tools, and executive stakeholder management.